2-Undecanone

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2-Undecanone
IUPAC name

Undecan-2-one

Other names

Methyl nonyl ketone (MNK)
Nonyl methyl ketone
Methyldecananone
2-Hendecanone
Undecanone
IBI-246

Identifiers
CAS number 112-12-9 YesY
ChemSpider 7871 YesY
UNII YV5DSO8CY9 YesY
DrugBank DB08688
KEGG C01875 YesY
ChEBI CHEBI:17700 YesY
RTECS number YQ2820000
Jmol-3D images Image 1
Properties
Molecular formula C11H22O
Molar mass 170.29 g mol−1
Appearance Colorless or pale yellow liquid
Density 0.829 g/cm³, liquid
Melting point 15 °C; 59 °F; 288 K
Boiling point 231 °C; 448 °F; 504 K
Solubility in water 0.00179 g/100 mL (25 °C)
Hazards
MSDS External MSDS
EU classification Flammable (F)
Irritant (Xi)
R-phrases R50 R51
S-phrases S23 S24 S25
NFPA 704
2
1
0
Flash point 88 °C; 190 °F; 361 K
Related compounds
Related Ketones Acetone
Butan-2-one
3-pentanone
 YesY (verify) (what is: YesY/N?)
Except where noted otherwise, data are given for materials in their standard state (at 25 °C (77 °F), 100 kPa)
Infobox references

2-Undecanone, also known as methyl nonyl ketone and IBI-246, is an oily organic liquid manufactured synthetically, but which can also be extracted from oil of rue. It is found naturally in bananas, cloves, ginger, guava, strawberries, wild-grown tomatoes, and the perennial Houttuynia cordata.[1]

Uses

2-Undecanone is used in the perfumery and flavoring industries, but because of its strong odor it is primarily used as an insect repellent or animal repellent. Typically, 1–2% concentrations of 2-undecanone are found in dog and cat repellents in the form of a liquid, aerosol spray, or gel.

Research from North Carolina State University has shown that it may be useful as a mosquito repellent, as effective as, or even more effective than, DEET.[2][3]

Chemical properties

2-Undecanone is a ketone that is soluble in ethanol, benzene, chloroform, and acetone, but its large carbon chain renders it insoluble in water. Like most methyl ketones, 2-undecanone undergoes a haloform reaction when in the presence of a basic solution of hypochlorite. For example, the reaction between 2-undecanone and sodium hypochlorite yields sodium decanoate, chloroform, and sodium hydroxide.

CH3CO(CH2)8CH3 + 3 NaOCl → CH3(CH2)8COONa + CHCl3 + 2 NaOH

See also

Notes

  1. ↑ Liang, Minmin et al.; Qi, M; Zhang, C; Zhou, S; Fu, R; Huang, J (2005). "Gas chromatography–mass spectrometry analysis of volatile compounds from Houttuynia cordata Thunb after extraction by solid-phase microextraction, flash evaporation and steam distillation". Analytica Chimica Acta 531 (1): 97–104. doi:10.1016/j.aca.2004.09.082. 
  2. ↑ Mosquitoes Repelled By Tomato-Based Substance; Safer, More Effective Than DEET, Science Daily, June 2002
  3. ↑ Stephen J. Toth, Jr. and Wayne G. Buhler (2002). "North Carolina State University Scientist Discovers Mosquito Repellent in Tomatoes". Pesticide Broadcast 12 (5). 

References

  • Lange's Handbook of Chemistry (14th Edition), McGraw-Hill, 1992; Section 1; Table 1.15
  • The Condensed Chemical Dictionary (10th Edition), Gesner G. Hawley
  • 2-Undecanone from The Good Scents Company
  • MSDS for 2-Undecanone
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